(Diethylamino)sulfur trifluoride → methyl 6-(2-fluorocyclohexyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1008989Notes

Reaction equation

HRID 1008989 reaction equation
C(N(S(F)(F)[F:7])CC)C.O[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17]1[C:18]2[S:24][C:23]([C:25]([O:27][CH3:28])=[O:26])=[CH:22][C:19]=2[NH:20][CH:21]=1.C([O-])(O)=O.[Na+]>CCOC(C)=O>[F:7][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17]1[C:18]2[S:24][C:23]([C:25]([O:27][CH3:28])=[O:26])=[CH:22][C:19]=2[NH:20][CH:21]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 67298624methyl 6-(2-hydroxycyclohexyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 67298952methyl 6-(2-fluorocyclohexyl)-4H-thieno[3,2-b]pyrrole-2-carboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Diethylaminosulfur trifluoride (1.2 eq.) was added at −60° C. to a 0.1M solution of methyl 6-(2-hydroxycyclohexyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate in dry EtOAc, and the mixture was stirred at this temperature for 1 h, then allowed to warm slowly to RT. Aq. NaHCO3-solution was added and the mixture was extracted with EtOAc; the organic layer was washed with water and brine, dried on Na2SO4 and concentrated. Chromatography (PE/EtOAc) afforded the title compound (73%). 1H-NMR (300 MHz, CDCl3, 300 K, δ) 8.31 (bs, 1H), 7.67 (s, 1H), 7.06 (s, 1H), 4.53 (dtd, 1H, J 48.6, 10.1, 4.5), 3.88 (s, 3H), 2.88-2.77 (m, 1H), 2.41-1.17 (m, 8H); MS (ES+) m/z 282 (M+H)+.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washthe organic layer was washed with water and brine
  3. customdried on Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-375c211d5a0c4fc8a6501713a8c48ab3
Source dataset
uspto-grants-2011_07
Patent number
US07973026B2

Reaction notes

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